Ethyl bromoacetate → HCID 13472327, compound

HRID 1248050Notes

Reaction equation

HRID 1248050 reaction equation
[CH:1]1([NH2:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CO>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][NH:10][CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[CH3:23]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 123445(+-)-1-Aminoindan

Product 1

HCID 13472327HCID 13472327, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 13.3 g of 1-indanamine in 100 ml of methanol are added 6.9 g of potassium carbonate and 16.9 g of ethyl bromoacetate, and the mixture is refluxed for 30 minutes. The reaction mixture is poured into 300 ml of ice-water, and subjected to extraction with 500 ml of ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure, and the residue is subjected to silica gel column chromatography and eluted with acetone-benzene (1:20) to give 9.0 g of N-(1-indanyl) glycine ethyl ester as a colorless oil. To this oil are added 5 ml of 20% alcoholic hydrochloric acid and 200 ml of ethyl ether, and the mixture is allowed to stand at room temperature to give 9.0 g of N-(1-indanyl)glycine ethyl ester hydrochloride as colorless needles. Melting point: 130°-132° C.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. extractionsubjected to extraction with 500 ml of ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. washeluted with acetone-benzene (1:20)

Sources & evidence

ORD record
ord-e117f20dfdf7421d9d8a7c29d6df4857
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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